Playing to Win
by princessblaine
Summary: Kurt Hummel is an out and proud Cheerio at McKinley High. When Santana Lopez bets that he can't get Blaine Anderson  resident nerd  to sleep with him before Prom, he accepts and sets about getting into Blaine's pants.
1. Chapter 1

Kurt Hummel prided himself on being who he was. A Cheerio, a fantastic singer and performer and completely open about his sexuality.

Being a Cheerio gave him protection from things like getting slushied and thrown into dumpsters, things that the other members of Glee club weren't so lucky to have. Except Santana and Brittany who were also on the Cheerios.

Up until two weeks ago, he was the only out gay kid at McKinley High. Blaine Anderson, a quiet boy who wore bow-ties and sweater vests, came out shortly after he transferred at the beginning of the year. Kurt was still confused about why someone would come out of the closet willingly while attending McKinley High. Kurt was more or less forced from it, with his voice and the way he dressed. The only person he'd ever had to come out to was his father, and that had been a struggle all on its own.

Kurt watched as Blaine opened his locker to shove his books inside and nearly jumped out of his skin when Santana appeared beside him out of no where. "You have got to stop doing that," he hissed while he opened his own locker.

"You need to be more careful with your leering," Santana said, leaning against the lockers. "Looking at Anderson like that will get you knocked to the bottom of the social pyramid, and I doubt you want that seeing as how look it took you to get to the top in the first place."

Kurt grimaced slightly remembering his Sophomore year. He had become well acquainted with slushy facials and the dumpsters outside the cafeteria. Junior year he had found the Cheerios and he'd been safe ever since.

There was a yelp from behind him, and Kurt turned on his heel. Blaine had just been covered head to toe in what looked like red slushy. Kurt closed his locker door and raised an eyebrow when he saw Santana smirking at him.

"What are you thinking about?" Kurt asked slowly. When Santana looked at him like that it never meant anything good.

Santana pulled out a nail file (and where did she even keep that in her Cheerios uniform?) and licked her lips. "I bet you can't get in Anderson's pants before prom night."

"Excuse you?" Kurt was not a virgin, one too many drinks at one of Puck's parties had seen to that during the summer. He'd had sex with Puck on more than one occasion since, but he'd never pursued someone for it specifically. "Come on, look at him. It's blatantly obvious that he's a virgin."

"Wouldn't that just be fantastic though? Kurt Hummel, head cheerleader gets the nerdiest kid at McKinley to give him his virginity? Suddenly, you're getting high-fives while Blaine Anderson becomes the laughing stock of the school. Unless of course you don't think you can get him to do it." Santana looked up from her nails and smiled smugly at him.

Kurt swallowed and turned to look back at Blaine who was brushing slush off his clothes. "You have a bet," he said as he faced Santana. "I will get Blaine Anderson to sleep with me before prom night. And when I do, I'm counting on you to give me the recognition I deserve."

"Good luck, Hummel. You're going to need it," Santana replied before she walked down the hall.

Kurt watched her leave before he tucked his bag over his shoulder and walked straight over to Blaine.

"Blaine Anderson?" Kurt questioned softly as he tapped Blaine on the shoulder.

Blaine froze under his touch and immediately caved in on himself. "Look, if you're going to take my lunch money or throw me into the lockers, just do it. There's no need to insult me and make matters worse while you're at it."

Kurt cleared his throat. "I was actually going to ask if you need any help."

Blaine turned slowly and Kurt had to stop himself from wincing at the amount of slush that was still covering Blaine's head and torso. "I have a favor to ask you, actually."

"No, I'm not going to complete your History assignment for you," Blaine replied smoothly. "It was set three weeks ago and you should have done it when you had the chance."

Kurt silently wondered exactly how many people had been asking Blaine to do their homework for them. "Um, no. Perhaps we should take this into the bathroom so we can get you cleaned up?"

Blaine nodded his head and the motion caused more slush to slide down his face. He quickly closed his eyes and Kurt gripped his hand, pulling him into the nearest washroom.

"Why are you doing this?" asked Blaine as Kurt dipped his head over the sink. "Last week you were the one throwing a slushy in my face and this week you're helping me clean it off. What's your angle here?"

Kurt reached for a cloth and wet it before moving it over Blaine's face. "I need your help. And not in the do my homework way," he clarified. "I'm failing History. If I don't raise my mark, I'm going to get kicked off the Cheerios and I can't let that happen."

It wasn't the worst lie he'd ever told, and if he was honest with himself it probably wouldn't be the only one. Over the next few months he'd have to coerce and lie his way into Blaine Anderson's bed. The reward would not only be sexually satisfying, but the popularity boost that came from it would be huge.

Kurt grabbed a dry towel from the racks and flung it over Blaine's head.

"You're asking me to tutor you?" Blaine said, a dumbstruck expression on his face. "What's in it for me?"

"You get to be seen with me on a daily basis and I'll make sure the slushy protection extends to you during the course of my tutoring. Sound fair?" Kurt dried off his own hand before he extended it to Blaine.

Blaine looked at it, his forehead scrunched up in confusion. He seemed to be fighting an internal battle before he reached out and grasped Kurt's hand. "The protection starts as soon as we leave the bathroom," Blaine said. "When do you want to start studying?"

Kurt shook Blaine's hand before he dropped his arm back to his side. "Come over tomorrow night. Finn's over at Rachel's or Quinn's and my dad is taking Carole out for dinner and a movie. We'll have the house to ourselves," he lowered his voice and was pleased when a blush crept up Blaine's neck.

"It's easier to study when there's silence," Blaine replies, voice higher than normal. "I mean, no distractions and what not."

Blaine stood up from his chair and nodded. "I'll meet you after school in the parking lot tomorrow. I have my own car so I'll just follow you home. Is that okay?"

Kurt smiled. "Yeah. That's great. See you in Glee club this afternoon, right?"

"Yeah. See you then." Blaine pulled open the door and fled the washroom.

Kurt leaned back against the wall and pulled out his phone, sending off a quick text.

**To: Satan**  
><em>Project get Blaine Anderson into bed is officially a-go.<em>


	2. Chapter 2

"Don't you dare throw that slushy, Noah!" Kurt yelled down the hall. Blaine was frozen in place, books already on the floor and Kurt spotted the white and red cup in Puck's hands. "Blaine is under Coach Sylvester's protection and if you throw that, you'll have her to deal with!"

Puck looked back at Kurt for a moment before he turned his body and threw the liquid at Jacob Ben Israel who was coming in the opposite direction.

Kurt closed the distance between them quickly and grabbed onto Puck's shoulder. "I mean it Puckerman. Blaine's not to be touched by you or any other members of the football team. Understand?"

Puck narrowed his eyes for a moment. "Are you hooking up with him or something, Hummel? Didn't realize you were picking from the bottom of the fishing pool."

"That doesn't even make sense," Kurt shook his head. "I'm failing a class and Blaine is tutoring me so I don't get kicked off the Cheerios. Go to class, Puckerman."

Puck made a movement towards Blaine that made him recoil into the lockers. "You got lucky this time, Anderson," he said before he joined the group of football players walking past.

Kurt watched as Blaine held his recently recovered books tighter to his body. "At least I got here before he actually threw it," he said. "But if we're being completely honest, I wouldn't have minded having to clean you off again. In the bathroom. Alone." Kurt smiled knowingly.

Blaine pushed up the glasses that were falling down his nose. "Thank you. Um, for the saving me thing. It was blueberry, I think. Not one of my favorites. Don't enjoy the taste of it as much as the cherry ones."

Kurt laughed softly and brought his hand to slide down Blaine's arm. "Well, if you ever need someone to lick blueberry slushy off of you, just let me know. I'd be more than willing to assist," Kurt dropped his voice an octave, pleased when Blaine visibly swallowed and ducked his head.

"I'm assuming we're still meeting after school then?" asked Blaine. "Seeing as we both have Glee after class-"

"No. I mean, Mr. Schuester already handed out the assignment so today it will just be Rachel fighting her way to perform first. Why don't we just go straight to my house after final class?" Kurt said warmly. "It'll give us more time to study."

Blaine sucked his bottom lip between his teeth before he lifted his gaze back up to Kurt's face. "Yeah. Sure. It's just one meeting."

* * *

><p>Kurt was pleased to see that his dad and Carole were both out of the house when he returned with Blaine. The last thing he wanted was to be interrogated about his new friend before he got through with the plan.<p>

"Nobody's home?" Blaine mumbled, eyes wide as he stepped into the entrance way.

Kurt nodded. "Carole and dad are probably out on a dinner date, and Finn is out with either Quinn or Rachel. I can never keep track of which one it is."

Blaine smirked. "Yeah, I know what you mean. Seems every week it's one or the other singing a love song to him or about him. So glad I don't have a boyfriend to worry about screwing things up with."

"No boyfriend?" Kurt questioned. He already knew the answer but it was an opening so he took it.

"Of course not. Look at me," Blaine gestured down to his wardrobe. "I'm not exactly the hottest guy at school. I focus in class, I wear these ridiculous thick framed glasses because my parents won't buy me anything less obnoxious and I happen to love bow-ties."

Kurt raised an eyebrow. "Your bow-ties..." he paused, thinking of the right word. "Interesting. It seems like you never wear the same one twice. I applaud that."

Blaine fiddled with the strap of his bag before Kurt motioned upstairs. "Shall we?"

They walked up in silence and Kurt pushed open the door of his bedroom. He waited for Blaine to step inside before he closed the door behind them.

Blaine cleared his throat. "You don't have a desk. Maybe we should go back downstairs?"

"We can work on my bed," Kurt said happily. "There's enough space for both of our books and both of us. I always find it easier to concentrate when I'm comfortable, don't you?" Kurt slid Blaine's bag off his shoulder and placed it on the bed. "I promise I don't bite," he paused and then continued. "Unless of course, you're into that sort of thing."

"I wouldn't know," replied Blaine. "Like I said, never had a boyfriend."

Kurt opened his mouth to reply but his phone began to ring. He forced it out of his pocket and grimaced when he saw that it was Santana. "I'll be right back. It's my dad."

He quickly walked out of the room and down the hall before he accepted the call. "What do you want, Santana?" Kurt hissed.

"_Someone's got their panties in a twist. Relax. I was just calling to see how things were going. I saw you two walk out together so I figured you probably tapped that already."_

Kurt pinched the bridge of his nose and exhaled. "Not yet. I haven't had a lot of time to get things going. But I will win this. And when I do, I have a little challenge of my own for you."

"_I'm listening."_

"Rachel Berry," Kurt said before he ended the call.

Kurt made his way back to his room quickly, surprised to see Blaine had already opened both of their books and was jotting down notes. "Hey, I thought you were supposed to be tutoring me. That usually means I have to be present for the assistance."

Blaine looked up and handed Kurt the sheet of paper he'd been writing on. "I took a peek at the notes you wrote down and it's no wonder you're having so much trouble. You have to keep it short and specific in order for your brain to keep the information for long periods of time. I simply shortened your notes and obviously made them more specific, so when the time comes for you to study, you'll have what you need and be able to retain the original information for a longer period of time."

Kurt sat down on the bed as he glanced over the new notes. He'd apparently missed more information than what he thought because Blaine had caught a whole slew of things that Kurt hadn't really thought important. "Wow, Blaine. This is a great start. I'm going to be passing History in no time at all."

Blaine clicked his pen and smiled proudly. "That's the idea."

They worked quietly for a few minutes. Blaine under-lined things in Kurt's textbook that he thought were relevant while Kurt went back and edited the previous notes he'd taken to make them better with Blaine's advice.

Purposely, Kurt sucked the tip of his pen into his mouth and watched Blaine from under his eyelashes. When he caught Blaine staring, he dropped his gaze back down to his notes and swirled his tongue over the tip of the pen.

Blaine's eyes darkened and the all too familiar flush appeared on his cheeks. He pursed his lips and looked back down at his work, his hand now scribbling faster than before.

Feeling a little more daring, Kurt reached forward and slid his hand up Blaine's thigh. Their eyes locked and Kurt squeezed the muscle gently with his fingertips. He let his thumb rub insistently over the clothed skin and he felt Blaine tense under his touch.

Blaine looked down at Kurt's hand and then back up, licking his lips. "I... I don't know-"

"Shh," Kurt whispered and leaned forwards. He pressed on Blaine's chest until he was laying flat on his back. "Have you ever been kissed?"

Blaine's tongue poked out of his mouth again, and Kurt watched as it slid from one side of his lips to the other. "I.. no. I- I haven't. I've never had a boyfriend."

Kurt looked into Blaine's eyes, the normal hazel almost completely darkened. This was incredibly easy, too easy. Just as Kurt leaned down to connect their lips, Blaine pushed on Kurt's shoulders and wiggled out from underneath him.

"I think that's good for today. I think we've covered enough. I've fixed your notes and you've fixed your own notes and I highlighted things that you should look out for and I just really think we're good for today. See you at school tomorrow, yeah?" Blaine said all in one breath as he packed his things into his bag.

Kurt stayed where he was and watched as Blaine walked out of the bedroom. He heard the noise of the front door opening and closing and then he collapsed onto his bed.

**To: Satan**  
><em>This might be a bit more difficult than I though it was going to be.<em>


	3. Chapter 3

Kurt walked up to Blaine just as he closed his locker door. "Blaine, I just wanted to-"

"Look, Kurt," Blaine said. "I've heard about you and Puck and how you," he blushed and looked at the floor before he returned his gaze to Kurt's face. "Did stuff."

"You mean had sex," Kurt deadpanned.

Blaine shuffled his feet and bit his lip. "Yeah, how you had sex. Kurt, I'm not like that, okay? I'm not just going to go hook up with someone because I've had too much to drink or it seems fun. I want sex to mean something. I've never even been kissed before and I want that to be special. Not with some cheerleader who wants it just because I'm convenient."

Kurt nodded along as Blaine spoke. "I understand that and I'm sorry. It's not just because you're convenient, I can promise you." Kurt pulled out the single yellow rose from behind his back and presented it to Blaine. "There was a reason I asked you to tutor me, Blaine. Instead of just some random geek. If I'm being completely honest, I've had a bit of a crush on you for awhile."

Blaine pushed his glasses up his nose and Kurt smiled at the flush that crept up his neck as he accepted the flower. "I'm going to be honest. I really have no idea what to say."

"Come out with me tonight," Kurt said as he rocked onto his heels. "We can go down to the park and watch the stars or something. That way you don't have to worry about me trying to have sex with you on my bed again."

Blaine brought the flower to his nose and sniffed once. Kurt took the moment to admire how long Blaine's eyelashes were as they fluttered against his cheek. "That sounds nice. I don't know why you even acknowledged my existence, but I appreciate it. I think you're a really nice person, Kurt. At least when you want to be."

Kurt ignored the pang of guilt as Blaine smiled at him. "Thank you, Blaine."

The bell rang above them, signalling that it was time to get to classes.

"I'll pick you up at 8, okay?" asked Kurt as he hooked his thumb onto his bag.

Blaine smelled the flower again before he nodded. "Yeah. I'll text you my address later. See you tonight, Kurt."

Kurt leaned against the lockers and watched Blaine as he walked away. It wasn't until the sound of a fist slamming into metal met his ears that he broke his line of sight to find Santana smirking at him.

"A rose? Really Hummel? Are you sure you're not actually starting to like Anderson?" Santana asked. "I mean, it's all fun and games right now and sure some people are talking, but if you're planning on dating him long term, you're looking at a fall down the food chain."

Kurt scoffed and rolled his eyes. "As if. I just want to win this bet. Plus, sex with a virgin is probably terrific. Not to mention, it will be nice to top for once."

Santana laughed. "By the way, I took you up on that thing you mentioned yesterday."

Kurt searched his brain but came up empty. "Pardon?"

"Rachel Berry? I've decided to go along with it and see if I can get her into bed before you get Anderson. Winner gets bragging rights. Seem fair?" Santana said and reached for Kurt's hand.

Kurt paused for a moment before he took it. "Seems fair. But Berry's still tripping over my brother Finn so I doubt you'll have much luck." Kurt tilted his head down the hall.

Rachel was in the middle of a pretty intense lip lock with Finn and Santana pursed her lips.

"I'm not concerned. I heard she used to make love eyes at Quinn during Glee Club so I doubt her dating that bag of potatoes is going to be much of a problem. Don't worry about me, lady lips. I've got this covered. Be more worried about your little problem because I don't think he's going to put out within the next few weeks."

Kurt looked back down the hall where Blaine had disappeared before he shrugged. "I've just got to woo him beforehand. He wants to be wined and dined. Like I did before Puck and I hooked up. He wants feelings and all that. I'll have him spread out on his back and begging for me within the next two weeks."

As Kurt turned into Blaine's driveway, he ducked his head to admire the sheer size of Blaine's house. Before he could put much thought into it, Blaine pulled open the passenger door and hopped inside.

"I hope you weren't waiting long. I ended up showering for longer than expected and when I finished getting dressed I.. Kurt?"

Kurt blinked a few times. "I.. yeah no. I wasn't waiting long at all," he gestured to Blaine's hair. "You look good with it like that. Whatever you did to it. Looks good."

Blaine's hand instantly came up to pat at his curls. "I didn't have time to gel it like I usually do. I can go back in if you want. It'll only take a few minutes."

"No!" Kurt exclaimed and grabbed Blaine's arm before he could open the door. "I mean, no it's okay. You look really nice without the mountain of gel. You should, you know, wear it like that more often."

Blaine settled back into the seat, a satisfied smile on his face. "It makes me feel more comfortable at school," he said quietly, and Kurt turned down the radio to hear him better. "At least if it's all gelled down, there's nothing for the football players to yank as they're walking by. Just my books and occasionally my glasses if they're feeling especially cruel."

Kurt listened intently as Blaine spoke, his fingers wrapped tightly around the steering wheel. "I'm sorry about them. Speaking of your glasses, where are they?"

"Um, I have contacts. I figured since we're going to the park and it's dark, if they get knocked off my face I wouldn't be able to find them so it was a safe choice to just put in my contacts," Blaine replied.

Kurt cleared his throat as he turned into the parking lot. "Well, you look good without your glasses. You look good with them too, I mean the whole hair down and contacts just makes you look even better."

He wasn't lying this time. Blaine looked down right delectable in his tight black jeans and his fitted sweater. Kurt took longer to get out of the car just so he could look at Blaine's ass as they exited the vehicle.

"If you wanted to stare at my ass, you could have just let me walk in front of you," Blaine said over his shoulder as they walked towards the park.

Kurt's fingers tightened on the keys in coat pocket. "It's sort of hard not to miss, Anderson."

Blaine sat down on a swing and gave himself a push with his feet. "So, Cheerio Kurt Hummel, tell me about yourself."

Kurt pulled a piece of tissue paper from his pocket and wiped down the seat before he sat down on the swing beside Blaine. "Don't look at me like that. These are white pants and I don't want to ruin them."

"Okay, okay. Tell me some stuff about you that I don't already know," Blaine said. "Which is basically your name, age, that you're a Cheerio, you're failing History and you have a step brother named Finn Hudson," he paused. "Oh, and that you're a bit of a fashion fanatic."

Kurt laughed softly, pumping his legs as he started swinging. "Did you know that I used to have a crush on Finn? That was a very interesting few months. I actually hooked my dad up with his mom originally so that I could get closer to Finn." Kurt looked over at Blaine. "I was actually pretty selfish. But as it turned out, they hit it off and ended up getting married. Long after my crush on Finn had dissipated."

Blaine crossed his ankles and tucked his legs under him, the swing moving back and forth slowly. "So aside from Puck, Finn's the only other guy you've ever had a crush on?"

"Oh no. There was Sam," Kurt said with a small shake of his head. "I thought he was gay and he was attractive so naturally I made a move. Don't laugh at me okay. He dyed his hair and at the time I didn't think straight guys did that."

"So basically you've had a bad habit of falling for straight guys," Blaine clarified. "And how exactly did you end up hooking up with Noah Puckerman?"

Kurt dug his boots into the dirt to stop the motion of the swing. "The first time it happened over the summer. Rachel threw a party and I had one too many. Figured why the hell not when Puck stumbled over to me, all tequila breath and bad footing. Someone like me doesn't find love in a small town."

He blinked back the pool of tears that threatened to spill from his eyes and continued speaking. "After that, it was sort of easy to just go back to it, you know? Yeah sure, it was Noah but it was what I was used to so why not? I thought no one would ever want me that way, so really what did I have to lose?"

Kurt jumped when he felt a hand on his shoulder and then Blaine's fingers intertwined with his. Blaine pulled him from the swing and towards the grass.

"Blaine, what are you doing?" Kurt asked as Blaine directed them to the centre of a soccer field.

Blaine moved in close and wrapped a hand around Kurt's waist and brought them closer together until Kurt could feel Blaine's body heat through their layers. "Dancing with you."

Kurt's hand came to rest on Blaine's upper arm. "There's no music," he said quietly.

Blaine began to hum right beside Kurt's ear and Kurt couldn't help but laugh. "Teenage Dream by Katy Perry? Really?"

"Shh," Blaine urged. "Just dance."

The height difference was a little weird, but Kurt let his head fall to Blaine's shoulder as they moved in small circles. His eyes drifted close as Blaine began to sing, and for a few moments he pretended that this was real. That he and Blaine might actually be able to be something.

"_We can dance, until we die_

_You and I, will be young forever."_

The sudden stop of movement made Kurt lift his head and look at Blaine with concerned eyes. "Everything okay?"

Blaine's eyes sparkled even in the dark. "Everything's perfect."

Kurt's eyes drifted down to Blaine's lips. "I want to kiss you."

"I might be bad at it," Blaine whispered. His tongue slipped out to wet his lips, and his eyes locked on Kurt's.

"Did you seriously just quote A Walk to Remember?" Kurt teased.

Blaine slid his hand down Kurt's arm and slotted their fingers together. "It's a good movie."

"It is," Kurt answered. He hesitated for only a second more before he dipped his head and kissed Blaine on the lips.

It turned out that Blaine was anything but bad at kissing. His lips moved effortlessly against Kurt's and when his tongue slipped along Kurt's bottom lip, it became very obvious that Blaine was _really _good at kissing.

Only when Kurt emitted a tiny moan did Blaine pull back, eyes dark and cheeks flushed. "We should, um, get back. It's getting late and it's a school night."

Kurt took a step back and they walked back to the car in a comfortable silence. When Blaine linked their hands in the car, Kurt made sure to give a reassuring squeeze.

"I had a great time tonight, Kurt," Blaine said when Kurt pulled up in front of Blaine's house. "See you tomorrow after school?"

"Yeah. I'll make sure to grab History text book before I leave. Did you want to study at my house again?" Kurt said.

Blaine thought for a moment before he answered. "We can come back to my house? My dad is away on business and my mom is on vacation so we don't have to worry about an interruption or anything."

Kurt smiled. "That sounds great. See you tomorrow, Blaine."

Blaine closed the door and walked up the path, waving goodbye before he stepped into the house.

Kurt sunk back into his seat and grabbed his phone from the console.

**To Satan:**

_Those bragging rights are going to be great to have._


End file.
